WO2006016829A1 - Controlled-release formulation comprising tamsulosin hydrochloride - Google Patents
Controlled-release formulation comprising tamsulosin hydrochloride Download PDFInfo
- Publication number
- WO2006016829A1 WO2006016829A1 PCT/PL2005/000052 PL2005000052W WO2006016829A1 WO 2006016829 A1 WO2006016829 A1 WO 2006016829A1 PL 2005000052 W PL2005000052 W PL 2005000052W WO 2006016829 A1 WO2006016829 A1 WO 2006016829A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formulation according
- matrix
- fatty
- tamsulosin
- tablet
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
- A61K9/2846—Poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
Definitions
- Controlled-release formulation comprising tamsulosin hydrochloride
- This invention relates to a solid oral con ⁇ trolled-release formulation comprising tamsulosin hy ⁇ drochloride.
- Tamsulosin (-) - (R) -5- [2- [ [2- (o- ethoxyphenoxy)ethyl]amino]propyl] -2- methoxybenzenesulfonamide monohydrochloride, is a se ⁇ lective, competitive antagonist of type exIA post ⁇ synaptic adrenergic receptors in the prostate, used to treat the symptoms of benign prostatic hyperplasia. Due to its pharmacokinetic properties, tamsulosin hydrochloride is administered to the patients in the form of an oral, controlled-release formulation, suit ⁇ able for a once-daily administration.
- the formulation that has been brought into the medical practice under the brand names Flomax ® , Omnic ® and Harnal ® is a capsule comprising pellets of tamsu ⁇ losin hydrochloride 0.4 mg with methacrylic acid co ⁇ polymer and microcrystalline cellulose as the main in ⁇ active ingredients.
- EP 0533297 Al and EP 0194838 Al there is disclosed the composition of particles, from which tamsulosin is gradually re ⁇ leased due to the use of a matrix of a macromolecular, water-insoluble release controlling agent selected from acrylic acid polymers and acrylic acid copolymers.
- This release controlling agent is used as an aqueous suspen ⁇ sion or emulsion or as a solution in an aqueous-organic system and acts also as a binder in the granulation step.
- Microcrystalline cellulose used as a carrier, constitutes at least 50 % by weight based on the weight of the formulation, and provides, on granulation, the cohesive particles.
- the particles containing tamsulosin hydrochloride are formed into tablets, capsules or granules. It is believed that the composition disclosed in EP 0533297 Al covers the commercially available cap ⁇ sules Flomax ® .
- methacrylic acid polymers and co ⁇ polymers are recently raising fears concerning safety of mucous membranes of the gastrointestinal system. Therefore, their gradual withdrawing or at least, lim- iting exposure of patients to these compounds seems to be well grounded.
- Appropriate extent of gelling is achieved by using a hydrophilic substance that is dissolved in the amount of water not exceeding 5 ml (per 1 g of the active in ⁇ gredient) , such as polyvinylpyrrolidone, D-sorbit or PEG 6000, in combination with a hydrogel-forming poly ⁇ mer characterized by average molecular weight over 2,000,000 or by viscosity of a 1% solution not less than 1,000 cPs.
- a hydrophilic substance that is dissolved in the amount of water not exceeding 5 ml (per 1 g of the active in ⁇ gredient) , such as polyvinylpyrrolidone, D-sorbit or PEG 6000, in combination with a hydrogel-forming poly ⁇ mer characterized by average molecular weight over 2,000,000 or by viscosity of a 1% solution not less than 1,000 cPs.
- This objective has been achieved by developing a solid oral controlled-release formulation in the form of enteric-coated tablets, exhibiting a dissolution profile of tamsulosin hydrochloride, as measured in a Type II paddle apparatus in accordance with the disso ⁇ lution testing method specified in the European Pharma ⁇ copoeia at 37 ⁇ 0.5°C and 100 rpm in a 0.1 N HCl buffer for 2 hours, followed by pH 7.2 buffer for the rest of test: 10-40% during first 2 hours (in HCl) ,
- the present invention relates to an enteric coated tablet formulation for a controlled release of tamsulosin hydrochloride wherein an active substance is homogenously dispersed within a matrix consisting of a mixture of fatty component and hydrophilic component, together with at least one diluent and optionally other pharmaceutically acceptable excipients.
- the fatty component of the matrix can be natural or synthetic substances selected from the group con ⁇ sisting of long-chain fatty acids Ci2 ⁇ c l8' glycerides of medium- and long-chain fatty acids Cg-C ⁇ g; hydrogen- ated fatty oils such as castor oil; hydrogenated leci ⁇ thins or the mixtures thereof.
- the fatty component of the matrix is a glyceride of a fatty acid, such as glycerol palmitostearate, glycerol monostearate, glycerol behenate.
- a fatty acid such as glycerol palmitostearate, glycerol monostearate, glycerol behenate.
- the most preferred fatty component of the matrix is glycerol behenate.
- Glycerol behenate such as commercially available Compritol 888 ATO, is a natural product being a mixture of 12-18% of mono-, 52-54% of di- and 28-32% of triglycerides of docosanoic acid (over 87% of the fatty acid fractions) .
- Glycerol behenate and other glyc ⁇ erides of fatty acids are used as tablets and capsules diluents and, in lower concentration, as lubricants. They may also form lipophilic matrixes for sustained release tablet and microsphere formulations.
- the content of the fatty component of the matrix in the formulation of the invention is 20-40% by weight based on the weight of the tablet's core.
- the hydrophilic component of the matrix can be any pharmaceutically acceptable inert substance that would allow for penetration of water into the tablet's core, thereby swelling, gelling or thickening and form- ing a viscous layer facilitating the diffusion of an active substance.
- Suitable components of this type com ⁇ prise, e.g. polyvinylpyrrolidone, polyvinyl alcohols, polyethylene glycols, ethers and esters of cellulose, preferably hydroxypropylmethylcellulose, sodium car- boxymethylcellulose, alginates and the mixtures thereof.
- the hydrophilic component of the matrix is polyvinylpyr ⁇ rolidone, in particular polyvinylpyrrolidone of a mo- lecular weight within the range of 25,000 to 300,000. Particularly preferred is polyvinylpyrrolidone of a mo ⁇ lecular weight about 50,000.
- polyvinylpyrrolidone is also a binding agent.
- the content of the hydrophilic component in the tablet's core depends on the type of the substance used. In case of polyvinylpirrolidones, their content depends on their molecular weight and solubility asso ⁇ ciated therewith as well as on other physical proper- ties. It could be selected by those skilled in the art on the basis of PVP characteristics and a common knowl ⁇ edge.
- polyvinylpyrrolidone of a mo ⁇ lecular weight about 50,000 its fraction is preferably 5-12% by weight based on the weight of the tablet's core.
- the assumed profile of controlled-release of tam- sulosin hydrochloride is achieved at the weight ratio of the fatty and hydrophilic components of the tablet's core within the range from 2:1 to 6:1, preferably at about 4:1.
- the core of the formulation according to the in ⁇ vention further comprises at least one diluent that can be any substance increasing the bulk of the tablet.
- at least one diluent that can be any substance increasing the bulk of the tablet.
- two different diluents of complementary properties are used, one of them facilitating penetration of water into the tablet's core while the other provides its skeleton.
- Appropriate diluents can be selected from the group consisting of sugar alcohols such as mannitol, sorbitol, xylitol or maltitol; sugars such as glucose, lactose, levulose, sucrose, maltose, glucose and dex ⁇ trose; starches such as corn starch and potato starch; cellulose derivatives such as microcrystalline cellu- lose; cellulose acetate; colloidal silica; calcium sul ⁇ fate; di- and tribasic calcium phosphate; calcium car ⁇ bonate; non-pareils; talc and other.
- sugar alcohols such as mannitol, sorbitol, xylitol or maltitol
- sugars such as glucose, lactose, levulose, sucrose, maltose, glucose and dex ⁇ trose
- starches such as corn starch and potato starch
- cellulose derivatives such as microcrystalline cellu- lose
- cellulose acetate
- Preferred diluents in the formulation according to the invention are the combination of sorbitol and lactose.
- Sorbitol, 1,2,3,4,5, 6-haxanehexol is used as a diluent in tablet formulations prepared by either wet granulation or direct compression.
- Sorbitol, available in an amorphous form as well as in four crystalline po- lymorphic forms, provides the bulk of the tablet and facilitates the erosion of the core skeleton by water.
- Lactose (O- ⁇ -D-galactopyranosyl- (1 ⁇ 4) - ⁇ -D- glucopyranose) , that is less soluble in water than sor ⁇ bitol, is widely used as a filler or diluent in tablets and capsules. It is available in two anomeric forms, ⁇ and ⁇ , among which ⁇ -lactose is anhydrous whereas ⁇ - lactose may be anhydrous or hydrated, having various distribution of molecular weight and flow characteris ⁇ tics. In the formulation according to the invention, lactose monohydrate is preferred due to its highly po ⁇ rous structure and a large specific area.
- the core of the tablet according to the invention can further comprise other pharmaceutically acceptable excipients that facilitate the manufacturing process and provide required physical and mechanical properties of the tablet .
- the additional excipients could be fur ⁇ ther components of the matrix, such as cellulose de ⁇ rivatives or acrylic polymers; binders such as prege- latinized starch; sodium alginate, polyvinyl alcohol, acacia gum; disintegrants such as methylcellulose, low- substituted hydroxypropylcellulose, sodium carboxy- methylcellulose, calcium carboxymethylcellulose, guar gum, crosspovidone, sodium croscarmellose, colloidal silicon dioxide, alginic acid, potassium polyacryline, sodium starch glycolate; hydrophobic agents such as waxes; preservatives; colorants and other substances, as needed.
- the present invention relates also to the process for the preparation of the controlled-release formula- tion of tamsulosin hydrochloride, which process com ⁇ prises:
- the additional excipients may be added to the composition of a core either before preparing granules containing the active ingredient or to the granules di ⁇ rectly before compressing into the tablet cores.
- lubricant (s) , glidant(s), additional fill- ers and binders, if any, are being admixed with the dry granules directly before compressing into the tablet cores.
- colloidal silicon dioxide, magne ⁇ sium trisilicate, starch, powdered cellulose, tribasic calcium phosphate or talc may be used, which can also play a role of the lubricant.
- the lubricants can also be calcium stearate, magnesium stearate, zinc stearate, sodium lauryl fumarate, hydrogenated castor oil, hydro- genated vegetable oil and others.
- Many of the excipients may play more than one function in the formulation according to the invention.
- the additional fillers in the com ⁇ pression process can be the same that are used to form granules or some other substances.
- sorbitol instant is used as the filler with hydrophillic proper ⁇ ties.
- the content of tamsulosin hydrochloride in the solid oral formulation according to the invention is 0.4 mg or its multiplicity per the unit dosage form.
- the formulation comprises about 0.2 wt % of tamsulosin hy ⁇ drochloride, 20-40 wt % of a fatty component and 5-12 wt % of a hydrophilic component of the matrix, based on the weight of the tablet's core,- made up to 100% with diluents and other excipients.
- the core of a tablet contains, in wt % of the core, 0.2 % of tamsulosin hydrochloride, 20-40 % of glycerol behenate, 5-12 % of PVP, 20-40% of lactose, 30-50 % of sorbitol (powder and instant forms combined) and 0.5-1.5 % of magnesium stearate, up to make 100%.
- the core of the tablet is protected by a coating resistant to gastric fluids and dissolving only in the neutral to weakly alkaline medium of an intestine.
- the coatings of this type are described, for example, in Pharmaceutical Dosage Forms and Drug Delivery Systems, H.C. Ansel, I.V. Allen, N.G. Popovich, 7 th ed. (1999), Lippincot, Williams&Wilkins.
- the acid resistant coat ⁇ ings are formed by anionic polymers and copolymers of acrylic acid or methacrylic acid, with (meth) acrylic acid esters, in particular copolymers of methacrylic acid with methyl methacrylate with free acid units; phthalates such as, e.g.
- cellulose acetate phthalate cellulose polyacetate phthalate, acetylvinyl polyphtha- late, acetylcellulose succinate, copolymers of vinyl acetate and crotonic acid, together with additives such as plasticizers, fillers, dispersing agents, col ⁇ orants and polishing agents.
- the appropriate dissolution profile of tamsulosin hydrochloride in the targeted place of gastro ⁇ intestinal tract is achieved by covering the cores with copolymers of methacrylic acid and esters thereof, such as those known under the trade name Eudragit, for exam ⁇ ple, Eudragit SlOO or Eudragit L 30 D-55 or the mix- tures thereof.
- Eudragit L 30 D-55 is a water dispersion of a copolymer based on methacrylic acid and acrylic acid ethyl ester with the ratio of free carboxyl groups to the ester app. 1:1.
- Eudragit S 100 is a copolymer of methacrylic acid and methacrylic acid methyl ester with the ratio of free carboxyl groups to the ester app. 1:2 and it needs to be partially neutralized with aqueous ammonia before coating the cores.
- the coating is 2-12 % by weight of the tablet core.
- the solid oral controlled-release formulation of tamsulosin hydrochloride in the form of enteric-coated tablet according to the invention is characterized by appropriate physicochemical parameters and by an ade- quate release profile of the active ingredient in vi ⁇ tro.
- the dissolution profile of tamsulosin hydrochlo ⁇ ride from the formulation has been measured in a Type II paddle apparatus in accordance with the dissolution testing method specified in the European Pharmacopoeia at 37+0.5°C and 100 rpm in two steps:.
- each time adjusting volume in each vessel to 500 mL with a phosphate buffer having the same pH and temperature.
- R ⁇ - mean percent active ingredient dissolved of the reference product
- T ⁇ - mean percent active ingredient dissolved of the formulation according to the invention.
- the similarity factor f2 for the tablets accord ⁇ ing to the invention was found to be about 70.
- the dissolution profiles of the tablet formulation according to the invention and the reference product Omnic ® capsules are similar.
- the solid preparation according to the invention provides appropriate in vitro dissolution profile of tamsulosin hydrochloride.
- the excipients have been sieved, if needed, through a 0.5 mm sieve.
- Lactose, powdered sorbitol and Compritol ATO 888 were stirred for 4 min. at the speed of a planetary-motion paddle of 300 rpm, until a uni ⁇ form powders blend was obtained.
- a suspension for granulation was prepared by dispersing tamsulosin hy ⁇ drochloride (1 wt% excess with respect to the calcu- lated amount), after sieving it through a 0.3 mm sieve, in water (40 mL per 10,000 tablets) . After emptying, the reactor was washed with 50 mL of water that was added to the suspension.
- the suspension was added to the mixture in the granulator.
- Granulation has taken 16 min. at 300 rpm of the planetary-motion paddle and 1,500 rpm of the high-speed propeller. After 8 min. of stirring, speed of the propeller was increased to 3,000 rpm.
- the granules, obtained this way were dried in a fluidized-bed dryer at 30 0 C for 8 min., to reach mois- ture content 0.5-2.0 wt%, and then particle size of the granules was standardized using an oscillating granula- tor provided with a 0.8 mm sieve. After standardiza ⁇ tion, granules were weighed.
- Necessary amounts of mag ⁇ nesium stearate and sorbitol instant were calculated on weight of the granules. Weighed amounts of both sub ⁇ stances, after careful blending in a barrel-shape blender (15 min., 15 rpm), were added to the granules and the mixture was carefully blended and then com ⁇ pressed on a rotary tableting machine, using 8 mm bi- convex punches and controlling the weight of the tab ⁇ lets.
- the tablet cores obtained as above, after deter ⁇ mining their weight, hardness, friability and dissolu ⁇ tion rate, were de-dusted and coated in a pan coater, pre-heated to app. 40 0 C.
- the coating suspension com ⁇ prising (in mg/500 mg) :
- the coating process was carried out in a pan coater at a temperature of the tablet bed 40 0 C, until a uniform coating, 10-12 mg per tablet, was obtained. Af ⁇ ter completion of coating, the tablets were tentatively- dried for about 30 min. , by slowing down revolutions of the coater's drum and lowering air temperature at the inlet to 40-50 0 C. The tablets, spread loosely on trays, were dried in a tray drier for 2 h at 40 0 C.
- Titanium dioxide 2.5 g Y Yeellllooww llaakkee 0.39 g.
- the cores have been placed in the drum of the pan coater and de-dusted.
- the bed of the cores has been heated up to about 30-34 0 C with inlet air temperature
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- General Chemical & Material Sciences (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/573,562 US20070298101A1 (en) | 2004-08-12 | 2005-08-12 | Controlled-Release Formulation Comprising Tamsulosin Hydrochloride |
EP05774341A EP1784161B1 (en) | 2004-08-12 | 2005-08-12 | Controlled-release formulation comprising tamsulosin hydrochloride |
PL05774341T PL1784161T3 (en) | 2004-08-12 | 2005-08-12 | Controlled-release formulation comprising tamsulosin hydrochloride |
DE602005004164T DE602005004164T2 (en) | 2004-08-12 | 2005-08-12 | FORMULATION WITH CONTROLLED RELEASE CONTAINING TAMSULOSINE HYDROCHLORIDE |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PLP-369566 | 2004-08-12 | ||
PL369566A PL204079B1 (en) | 2004-08-12 | 2004-08-12 | Oral solid tamsulozine hydrochloride preparation with prolonged release and method for its manufacture |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006016829A1 true WO2006016829A1 (en) | 2006-02-16 |
Family
ID=35445840
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/PL2005/000052 WO2006016829A1 (en) | 2004-08-12 | 2005-08-12 | Controlled-release formulation comprising tamsulosin hydrochloride |
Country Status (7)
Country | Link |
---|---|
US (1) | US20070298101A1 (en) |
EP (1) | EP1784161B1 (en) |
AT (1) | ATE382332T1 (en) |
DE (1) | DE602005004164T2 (en) |
PL (2) | PL204079B1 (en) |
SI (1) | SI1784161T1 (en) |
WO (1) | WO2006016829A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013082470A1 (en) * | 2011-12-02 | 2013-06-06 | Pegasus Laboratories, Inc. | Amphipathic lipid-based sustained release compositions |
US10722458B2 (en) * | 2011-12-02 | 2020-07-28 | Pegasus Laboratories, Inc. | Amphipathic lipid-based sustained release compositions |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030147950A1 (en) * | 2001-11-07 | 2003-08-07 | Platteeuw Johannes J. | Modified release tamsulosin tablets |
EP1413294A1 (en) * | 2001-07-27 | 2004-04-28 | Yamanouchi Pharmaceutical Co. Ltd. | COMPOSITIONS CONTAINING SUSTAINED−RELEASE FINE GRAINS FOR TABLETS QUICKLY DISINTEGRABLE IN THE ORAL CAVITY AND PROCESS FOR PRODUCING THE SAME |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8528195D0 (en) * | 1985-11-15 | 1985-12-18 | Boots Co Plc | Therapeutic compositions |
IT1289160B1 (en) * | 1997-01-08 | 1998-09-29 | Jagotec Ag | FULLY COATED PHARMACEUTICAL TABLET FOR THE CONTROLLED RELEASE OF ACTIVE INGREDIENTS WHICH PRESENT PROBLEMS OF |
US6395300B1 (en) * | 1999-05-27 | 2002-05-28 | Acusphere, Inc. | Porous drug matrices and methods of manufacture thereof |
US6500457B1 (en) * | 2000-08-14 | 2002-12-31 | Peirce Management, Llc | Oral pharmaceutical dosage forms for pulsatile delivery of an antiarrhythmic agent |
-
2004
- 2004-08-12 PL PL369566A patent/PL204079B1/en not_active IP Right Cessation
-
2005
- 2005-08-12 DE DE602005004164T patent/DE602005004164T2/en active Active
- 2005-08-12 SI SI200530197T patent/SI1784161T1/en unknown
- 2005-08-12 US US11/573,562 patent/US20070298101A1/en not_active Abandoned
- 2005-08-12 PL PL05774341T patent/PL1784161T3/en unknown
- 2005-08-12 WO PCT/PL2005/000052 patent/WO2006016829A1/en active IP Right Grant
- 2005-08-12 EP EP05774341A patent/EP1784161B1/en active Active
- 2005-08-12 AT AT05774341T patent/ATE382332T1/en not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1413294A1 (en) * | 2001-07-27 | 2004-04-28 | Yamanouchi Pharmaceutical Co. Ltd. | COMPOSITIONS CONTAINING SUSTAINED−RELEASE FINE GRAINS FOR TABLETS QUICKLY DISINTEGRABLE IN THE ORAL CAVITY AND PROCESS FOR PRODUCING THE SAME |
US20030147950A1 (en) * | 2001-11-07 | 2003-08-07 | Platteeuw Johannes J. | Modified release tamsulosin tablets |
Also Published As
Publication number | Publication date |
---|---|
EP1784161A1 (en) | 2007-05-16 |
EP1784161B1 (en) | 2008-01-02 |
SI1784161T1 (en) | 2008-06-30 |
PL1784161T3 (en) | 2008-05-30 |
PL204079B1 (en) | 2009-12-31 |
DE602005004164T2 (en) | 2008-12-11 |
PL369566A1 (en) | 2006-02-20 |
US20070298101A1 (en) | 2007-12-27 |
ATE382332T1 (en) | 2008-01-15 |
DE602005004164D1 (en) | 2008-02-14 |
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